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Mashable hosted its annual SummerMash event tonight – it was the third such entrepreneurial hob-knobbing event I have joined since moving back to San Francisco in March.

After receiving a free drink ticket from PubMatic for signing up for their iPod drawing, I set out to meet some other guests. The first dynamic duo I met were Adam and Braxton from Zannel, the Twitter of mobile phone rich media. By which I mean, they turn your mobile phone photos and video into micro-blog updates, the same way Twitter and FriendFeed do. Adam, Zannel’s CEO and a former McKinsey consultant, mentioned that users seemed to take a lot of photos of food, and we got into a conversation about how they might try to monetize that and other types of user content to build a real revenue stream for the micro-blog.

The second person I met was David Koehn of Phlooq, a stealth-mode social technology startup that connects individuals with the events and businesses they are fans of. Phlooq will enable a publisher like San Francisco’s 7×7 to tap into the social graph of a reader when he or she indicates what events she will be attending. I got a sneak-peak of the new app on David’s iPhone and from our conversation it sounded like the business was nearing the point of “unveiling.” I would say more, but then I would probably have to kill you…

Finally, I met Brendan Nee and his friend Justin, two young business partners working on an interesting new iPhone app which will help digest the powerful GPS data of local public transportation into a useful form. Using your phone’s own GPS signal, you could determine the best route from your current location to the destination of your choice using public transit, taking into consideration the current location of the busses, trains, and other vehicles in the network. The challenges confronting them, they explained, were two-fold:

First, getting MUNI and other public transit networks to share their data. Releasing this data would be potentially embarrasing to the transit authorities, since it could reveal just how often their services fail to arrive on time. Then again, argued Brendan and Justin, by sharing the data with an application like theirs, users would be better equipped to react and make alternative arrangements.

Second, how to monetize the application. If MUNI doesn’t even want to share the data in the first place, it would be a stretch to think that they would be willing to pay a software developer for delivering it in a user-friendly form to riders. We discussed alternatives, including helping public transit systems without GPS-enabled networks get online. The two could serve as a center of excellence in deploying the technology, and deliver the technology to analyze the GPS data on a fee-for-service basis to help the transit authority cut costs and optimize its network. They could then also push that proprietary data out to riders in the form of a application, perhaps with a small monthly fee.

SummerMash was a great event, even if the organizers didn’t quite manage to get the doors open on time. It’s nights like these that I will miss most after leaving the SF Bay.

Apple’s new MobileMe service, which will allow consumers to sync their mail, calendar, contacts, and other content across their phone, personal computer, and any other device which can access the web, has been been called “The Most Interesting part of this year’s WWDC” and heralded by some to be poised to “Crush Exchange and Google.” While the enthusiasm for a clean, integrated connectivity service is understandable, it exaggerates the willingness of consumers to pay for a service that, while imperfect in its implementation today, is almost entirely available today FOR FREE.

I don’t believe that MobileMe adds enough incremental value for consumers to be willing to shell out $99 – $149 per year for the ability to do what they can already. MobileMe is a service that is too expensive and too late.

Seamless connection of email between mobile and web? Try Gmail and its handy mobile application for the iPhone and Blackberry.

Photos hosted on your desktop and online? Try using Picasa Web plugins for iPhoto, or the Picasa application for PCs.

Getting this kind of functionality today does require that users plug the pieces together on their own. And it isn’t necessarily perfect. Admittedly, some of the features offered by MobileMe are not offered elsewhere – at least that I know about. For instance, constantly synchronized filing and sorting images and files (if I merge two albums in iPhoto, after both have been uploaded to Picasa Web, I have to duplicate that action on the Picasa website) and synchronized contacts (my BlackBerry integration with Lotus Notes or Outlook is perfect, but MobileMe, which is positioned as “Exchange for the rest of us,” is clearly targeting users that have neither) are both new and useful services, but are not justifiable at this price point.

Apple announced its new MobileMe service yesterday at the WWDC in San Francisco. The service is not yet available on Apple’s website (you can currently only sign up to be notified when it is ready), so I can only speculate as to its full functionality. MobileMe will replace its existing .Mac service. Given how weak customer enthusiasm had been for the original .mac service (which I also feel is largely due to its price relative to other offerings from Google and Yahoo), however, MobileMe’s heritage isn’t exactly a bragging right.

One reason MobileMe could win some users initially, however, is that consumers may rush in to claim valuable username real estate. “Mitch@Me.com” has a certain ring to it…

What do you think? Are MobileMe’s features enough to win consumers over? Will they be willing to fork out $100 for features that can essentially be pieced together for free online today?

When you are shopping, a sales person who can quickly understand your needs, preferences, and budget and make a reasonable, logical recommendation is invaluable. While shopping online has typically required that customers already know what they were looking for, or that they conduct extensive research online in advance of a purchase, software is increasing playing the role of the sales person. While approaches to providing customer shopping recommendations have evolved with time, however, today’s software leaves considerable room for improvement. The recent funding of a Bay Area startup focused on customer recommendation demonstrates that venture capitalists have started to wake up to the potential this technology could hold.

Consumer recommendation tools online initially began by mirroring something that already existed in the print world: editor’s reviews and “product of the year” comparisons. Later came “Buyer’s Guides” which followed a simplistic logic to evaluate a few short responses to an online survey to provide a customer recommendation. Then came Amazon‘s product recommendations, based upon the analysis of other customer decisions (“others who purchased this item also purchased…”). This basic methodology has since been implemented in a number of different places around the web, with varying success. I would argue that NetFlix has been the most successful – the one site where I have significant confidence in the accuracy of the recommendations I receive, and act upon them with little or no knowledge of the film recommended. NetFlix, unlike today’s iTunes or Amazon stores, however, does this by not only considered what I have purchased (or viewed) before, but also how much I liked it.

If other online stores were able to earn my trust to a similar level without requiring the lengthy initial interview NetFlix used to gauge my movie taste, and were able to more deeply understand my shopping parameters, tastes, and the reason I arrived at their site, they would stand to gain a greater share of my wallet. If Amazon had been able to successfully recommend a book to me which I enjoyed (rather than assuming the South American literature textbooks I bought for college courses indicate a passion for Spanish authors), I would be far more likely to trust their recommendations a second time, and to begin to rely upon this functionality, visiting their store on a consistent and regular basis.

Baynote, a software firm located in Cupertino, raised $10.75 million in a second round of funding last year from Steamboat Ventures. Its software attempts to understand customer intent by observing their actions on a website, and groups him or her into one of several customer archetypes to best deliver their anticipated needs. The challenge, however, is that a customer’s visit may be so short as to fail to give enough evidence of intent for the software to accurately predict their intent.

Richrelevance, a San Francisco based technology startup which yesterday announced it had closed a Series B round of investment valued at $4.2 million dollars backed by Greylock Partners and Tugboat Ventures, is attempting to deliver this kind of next-generation product recommendation software. Built by David Selinger, a leader from Amazon’s recommendations team, richrelevance promises the ability to enhance a web store by personalizing the shopping experience and providing relevant, high quality product recommendations. Unfortunately, however, its technology doesn’t appear to make any massive improvements upon the flawed system in place at Amazon.

Perhaps this shouldn’t be surprising, however. It turns out the challenge of substantially improving recommendation algorithms and technology is a very considerable one. Even NetFlix, which posed a large cash reward to the tune of $1 million for any person or team which could improve the accuracy of its prediction software by 10%, has been unable to meet this seemingly modest goal after over a year and a half.

I will watch with curiosity as other companies tackle this challenge. I believe it is a field with significant growth potential, and one where I would be excited to see more innovation and expansion. In the meantime, reasonably talented retail sales people need not worry about losing their jobs… just yet.

I am falling in love with “status messages” and “tweets.” These handy little messages tell me what my friends are up to, in a simple, usable way. It’s the best way for me to stay up to date on the day-to-day life of my friends and family (yes, even my mom is on Twitter). Plus, they help me keep track of where on earth all my friends are at any given time. This weekend, for instance, while in Cairo, I discovered a fellow Georgetown alum and colleague was also visiting for the weekend because of his Facebook Status message.

The shame of the current system of status messages is that they are incompatible. I have at least three places where I could / want to update my status – Facebook, Google Talk, and Twitter (most of you probably have 6 or more), but have to update each manually. Why don’t these services talk to one another? I should be able to set an automated import of my twitter messages to Facebook the same way this post will be imported as a Facebook “note” when it is published. My Google Talk status message should change every time I change my Twitter message, but if I update Google, Twitter should change.

Two players stand to benefit most from an increasingly “open” system of status messages (in my world, at least): Facebook and Twitter. Twitter is already wide open (For instance I can import my twitter messages via RSS into my personal blog at mitchellwfox.com) and is the natural host platform. If status messages are like ripples in my social network pond, spreading quickly to all networks, Twitter is well positioned to be the “stone.”

Facebook stands to benefit because status messages will be ever-more current, and more constantly changing. Because of the network effect of social networking, Facebook is the obvious place for me to go for “one stop shopping” of status messages. My profile will be more current, and my friends might even spend an extra second or two on Facebook before logging off to read what my status message is. Multiply that by hundreds of friends…

Anyway, I may be way behind the curve here. Is there already a way to do this? If so, tell me what it is!